A few episodes ago, Garrett Dimon shared the story of how he sold his SaaS product Sifter. In this episode, we complete the story arc by catching up with JD Graffam, the buyer and current owner of Sifter. JD is an agency owner who started buying SaaS product companies in 2012. We talk about how his background, how he got started buying businesses, and his approach to making deals and finding the right people to work with.

Relevant Links

JD's website
JD's Twitter
Simple Focus
Audience Ops
Sifter
Ballpark
Metalab
Garrett's Episode

In this episode, Jess and Jeremy chat with Radan Skorić, a long-time Ruby and Rails developer and team lead, co-organizer Ruby Zagreb, and author of the forthcoming book: Master Hotwire. We talk about Radan’s background in software, his discovery of Rails in the mid-2000s, technical blogging, writing a book, and technical aspects of Hotwire.

Related Links
Radan’s Blog
Radan’s Twitter
Book: Master Hotwire

This week, Jess and Jeremy get into the nitty-gritty of resource allocation for indie makers: how to make the most of your limited time, energy, and capital. As solo and small-team entrepreneurs, we constantly have to make tough calls about where to invest. It's not just about money; it's about what will actually move the needle.

They talk through the realities of running lean: how to balance building, learning, and staying sane along the way. From daily reading habits and favorite podcasts to managing information overload and keeping personal playbooks, they share the unpolished, behind-the-scenes strategies they use to grow without burning out.

If you’re bootstrapping, juggling roles, or just trying to make smarter bets with your time, this one’s for you.

In this episode of IndieRails, co-founders Ben Curtis and Joshua Wood share the origin story of Honeybadger, an application monitoring tool for Ruby on Rails applications (and many others).

They discuss their motivations for starting the company, the challenges they faced in the early days. The conversation also covers their approach to product development, marketing, pricing strategies, expanding into new markets and the lessons learned from their journey.

Honeybadger

Ben Curtis
Mastodon
Bluesky
LinkedIn

Josh Wood
Mastodon
Bluesky
LinkedIn

Our guest for this episode is Garrett Dimon. Garrett is a developer, author, conference speaker and multi time business owner. With some partners, he’s recently formed a company called “Very Good Software” where they own and operate several SaaS apps.
 
Garrett Dimon is a seasoned software developer and entrepreneur with a passion for front-end development and Ruby on Rails. His journey began in 1998, experimenting with HTML, CSS, and JavaScript before earning a Computer Science degree from the University of Texas at Dallas in 2000. Over the next eight years, he honed his skills in front-end development and information architecture through consulting roles with organizations of all sizes. During this time, he also shared his expertise through a column on front-end design and development for Digital Web Magazine.

In 2008, Garrett started his entrepreneurial journey and launched Sifter, a bug and issue tracking application built with Rails, which he ran until its successful sale in 2016. His experience building and selling Sifter inspired him to write and self-publish Starting and Sustaining, a book about building and running SaaS applications. After Sifter, Garrett took some time off from entrepreneurship and joined Wildbit and then egghead.

Eventually he went back on his own independent consulting where he helped clients Fireside.fm and Flipper. Little did he know that later on, he'd become part owner of these companies. In the fall of 2024 the one time business seller became the buyer. He, John Nunemaker, and Kris Priemer are operating Very Good Software, where fireside.rm and Flipper are core products.

Links:
GarrettDimon.com
BlueSky

Fireside.fm
Flipper
Very Good Software

Books

Recent podcast appearances:
Taking Over Fireside with John Nunemaker & Garrett Dimon
Master of Generators (with Garrett Dimon) | Dead Code

Our first-ever IndieRails guest returns to the podcast just shy of two years later. Joe Masilotti shares about niching down on Hotwire Native, changes in the related open source libraries, the direction of his consulting work, his parental leave last year, and the process of writing his forthcoming book, Hotwire Native for Rails Developers. (Special discount for listeners in the episode!)

Related Links
Twitter
Bluesky
Website
Hotwire Native for Rails Developers
Pragmatic Bookshelf page
Hotwire Native docs
Rails World 2023 Talk: Just enough Turbo Native to be dangerous

In this episode, Jeremy & I are excited to share a mic with Jim Remsik. Jim is the Founder and CEO of a digital agency called Flagrant. He is also a conference organizer…he created and hosts the popular Madison + Ruby conference. Jim has held many roles:  MC, speaker, developer, CEO, conference organizer, writer and many more, but I imagine most people know him as someone who is an all around awesome human.

Jim Remsik shares his journey through the tech industry, from his early days in software development to his transition from government work to agency life. He discusses building companies like Bendyworks and Flagrant, emphasizing how design and professional connections shaped his career path. The conversation follows his path from running Adorable to launching Flagrant, including the personal challenges he faced—health issues and navigating business during the pandemic. Jim reflects on the vital role of personal growth, team empowerment, and maintaining human connections in a remote-first world. Drawing from his agency experience, he shares how taking initiative and self-authorization were crucial to his entrepreneurial success. Throughout the discussion, Jim offers valuable perspectives on consulting and collaboration, emphasizing his core belief in actively supporting others' success. He explores the varied landscape of consulting work, industry uncertainties, and the power of personal mission statements. The conversation highlights how meaningful connections, purposeful work, and courageous leadership intertwine. Jim's guiding motto reveals how generosity and community-building shape his professional approach.

Show Links:

Socials

https://bsky.app/profile/jremsikjr.bsky.social

https://www.linkedin.com/in/jremsikjr/

Flagrant

https://www.beflagrant.com/team/

https://www.beflagrant.com/blog/author/jim-remsik/

Conferences

https://www.madisonruby.com/

https://rubyconf.org/about/

Posts

https://medium.com/authority-magazine/jim-remsik-of-flagrant-five-things-i-wish-someone-told-me-when-i-first-launched-my-business-or-14699acfbda2

https://www.beflagrant.com/blog/2024-predictions-2024-01-30

https://devops.com/the-ruby-on-rails-resurgence/

https://devops.com/the-ruby-on-rails-resurgence-2/

Other Podcasts

https://shows.acast.com/dead-code/episodes/all-those-letters-that-you-do-with-jim-remsik

https://www.codewithjason.com/podcast/14444689-211-jim-remsik-ceo-of-flagrant/

XO Ruby
https://bsky.app/profile/xoruby.com

Readalong - Practical Object-Oriented Design: An Agile Primer Using Ruby
https://app.thestorygraph.com/readalongs/5983b152-bf48-4ff3-aeb0-976ea67d0d08

Jess and Jeremy kick off the first recording of 2025 with a recap of 2024, and a look at their plans and goals for the new year. We chat about the importance of celebrating milestones, time management, financial planning, scaling development with business growth, and the cycles of sowing and reaping in our work.

Paul Campbell is a Rails developer (since v0.13), conference organizer, and the CEO and co-founder of Team Tito. Paul joins us to talk about his career building software, companies, and events. We chat about Paul's journey into programming, the risks and rewards of running conferences, finding his co-founder, and the opportunities that led to building Tito, Vito, and most recently, IO.

Relevant Links
Paul on BlueSky
Team Tito
Tito: event registration
Vito: online communities
IO: bespoke RSVPs

In this episode, we are joined by Barry Hess, James Adam, and Matthew Lettini from the Good Enough team to discuss their journey in creating a self-sustaining business built around meaningful, user-focused software. We explore the inception of their company and their latest product, Jelly—a shared inbox for teams. We dive into their experimental approach to business, their year of experimentation known internally as "Cosmic Maelstrom," the rollout of other products like their blogging software, Pika, and the decision to offer free tools. The team shares their insights into maintaining a human touch in customer support, navigating marketing challenges, and the value of brainstorming unconventional ideas. Through it all, they emphasize the importance of community, sustainability, and creating software that should exist in the world to make a meaningful impact.

Links:
Good Enough
Jelly
Pika
All Products

Good Enough Socials:
Newsletter
Mastodon
Bluesky
Threads
X

James
Matthew
Barry